#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/14/4101497.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4101497
loop_
_publ_author_name
'Wan, Xiaobing'
'Ma, Zhongxun'
'Li, Bijie'
'Zhang, Keya'
'Cao, Shaokui'
'Zhang, Shiwei'
'Shi, Zhangjie'
_publ_section_title
;
 Highly selective C-H functionalization/halogenation of acetanilide.
;
_journal_issue                   23
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7416
_journal_page_last               7417
_journal_paper_doi               10.1021/ja060232j
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C8 H8 Cl N O'
_chemical_formula_weight         169.60
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   'geom or difmap'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.516(2)
_cell_length_b                   9.5540(19)
_cell_length_c                   16.670(3)
_cell_measurement_reflns_used    5828
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.44
_cell_volume                     1674.9(6)
_computing_cell_refinement       Rapid-AUTO
_computing_data_collection       'Rapid-AUTO (Rigaku,2000)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC,2000)'
_computing_molecular_graphics    'Siemens SHELXTL V4.2,(Sheldrick,1990)'
_computing_publication_material  SHELXL-97,(Sheldrick,1997)
_computing_structure_refinement  SHELXL-97,(Sheldrick,1997)
_computing_structure_solution    SHELXS-97,(Sheldrick,1997)
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku RAXIS RAPID IP'
_diffrn_measurement_method       Ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0580
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5828
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.44
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.395
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
                                  HIGASHI, T. (1995). Abscor-Empirical
                                  Absorption Correction based on Fourier
                                  Series Approximation.
                                  Rigaku Corporation,Tokyo,Japan.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0053(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     105
_refine_ls_number_reflns         1465
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.936
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0200P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0663
_reflns_number_gt                776
_reflns_number_total             1465
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja060232jsi20060112_062552.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4101497
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.96758(6) 0.19712(7) 0.73117(4) 0.0743(3) Uani 1 1 d .
O1 O 0.77707(15) -0.21268(17) 0.59491(11) 0.0775(6) Uani 1 1 d .
N1 N 0.84393(18) 0.01140(19) 0.60963(10) 0.0417(5) Uani 1 1 d .
HN H 0.8212(19) 0.0970(19) 0.6097(10) 0.041(7) Uiso 1 1 d .
C1 C 1.0419(2) 0.0650(2) 0.67673(12) 0.0472(6) Uani 1 1 d .
C2 C 1.1695(2) 0.0428(3) 0.68913(15) 0.0650(8) Uani 1 1 d .
H2 H 1.2142 0.0986 0.7251 0.078 Uiso 1 1 calc R
C3 C 1.2305(3) -0.0621(3) 0.64836(18) 0.0785(9) Uani 1 1 d .
H3 H 1.3164 -0.0785 0.6577 0.094 Uiso 1 1 calc R
C4 C 1.1657(2) -0.1435(3) 0.59361(16) 0.0689(8) Uani 1 1 d .
H4 H 1.2078 -0.2140 0.5658 0.083 Uiso 1 1 calc R
C5 C 1.0380(2) -0.1197(2) 0.58039(13) 0.0516(6) Uani 1 1 d .
H5 H 0.9944 -0.1739 0.5432 0.062 Uiso 1 1 calc R
C6 C 0.9741(2) -0.0153(2) 0.62224(11) 0.0397(5) Uani 1 1 d .
C7 C 0.7549(3) -0.0864(3) 0.59502(13) 0.0501(6) Uani 1 1 d .
C8 C 0.6239(2) -0.0306(2) 0.57894(15) 0.0712(8) Uani 1 1 d .
H8A H 0.6250 0.0697 0.5825 0.107 Uiso 1 1 calc R
H8B H 0.5657 -0.0676 0.6179 0.107 Uiso 1 1 calc R
H8C H 0.5974 -0.0582 0.5262 0.107 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0672(5) 0.0779(5) 0.0778(5) -0.0334(4) 0.0046(4) -0.0163(4)
O1 0.0571(12) 0.0320(10) 0.1434(17) -0.0052(10) -0.0135(11) -0.0050(9)
N1 0.0391(12) 0.0283(11) 0.0576(12) -0.0004(10) -0.0071(10) -0.0005(11)
C1 0.0441(14) 0.0531(15) 0.0443(14) 0.0030(11) 0.0042(12) -0.0061(14)
C2 0.0424(16) 0.084(2) 0.0683(17) 0.0079(15) -0.0082(15) -0.0124(17)
C3 0.0403(17) 0.104(3) 0.091(2) 0.0279(19) 0.0029(18) 0.0064(18)
C4 0.0538(17) 0.0687(19) 0.084(2) 0.0110(16) 0.0202(16) 0.0163(19)
C5 0.0583(16) 0.0474(15) 0.0491(14) 0.0038(11) 0.0059(14) 0.0029(14)
C6 0.0409(14) 0.0383(13) 0.0398(12) 0.0076(11) 0.0008(12) -0.0047(13)
C7 0.0489(15) 0.0411(15) 0.0602(16) 0.0006(12) -0.0117(14) -0.0029(14)
C8 0.0506(18) 0.0582(17) 0.105(2) 0.0031(15) -0.0237(15) -0.0016(15)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 N1 C6 125.3(2)
C7 N1 HN 118.1(14)
C6 N1 HN 116.5(14)
C2 C1 C6 121.0(2)
C2 C1 Cl1 118.2(2)
C6 C1 Cl1 120.81(17)
C3 C2 C1 119.7(3)
C3 C2 H2 120.1
C1 C2 H2 120.1
C2 C3 C4 120.6(3)
C2 C3 H3 119.7
C4 C3 H3 119.7
C5 C4 C3 119.6(3)
C5 C4 H4 120.2
C3 C4 H4 120.2
C4 C5 C6 120.6(2)
C4 C5 H5 119.7
C6 C5 H5 119.7
C1 C6 C5 118.5(2)
C1 C6 N1 119.8(2)
C5 C6 N1 121.7(2)
O1 C7 N1 123.4(2)
O1 C7 C8 121.5(2)
N1 C7 C8 115.1(2)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.740(2)
O1 C7 1.229(3)
N1 C7 1.345(3)
N1 C6 1.409(3)
N1 HN 0.852(18)
C1 C2 1.374(3)
C1 C6 1.387(3)
C2 C3 1.370(3)
C2 H2 0.9300
C3 C4 1.379(3)
C3 H3 0.9300
C4 C5 1.379(3)
C4 H4 0.9300
C5 C6 1.390(3)
C5 H5 0.9300
C7 C8 1.500(3)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 HN O1 0.852(18) 2.106(19) 2.937(2) 165.1(18) 8_765
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 -1.3(3)
Cl1 C1 C2 C3 178.80(18)
C1 C2 C3 C4 1.5(4)
C2 C3 C4 C5 -0.6(4)
C3 C4 C5 C6 -0.5(3)
C2 C1 C6 C5 0.2(3)
Cl1 C1 C6 C5 -179.89(14)
C2 C1 C6 N1 -178.86(19)
Cl1 C1 C6 N1 1.0(3)
C4 C5 C6 C1 0.7(3)
C4 C5 C6 N1 179.8(2)
C7 N1 C6 C1 -144.1(2)
C7 N1 C6 C5 36.8(3)
C6 N1 C7 O1 3.7(4)
C6 N1 C7 C8 -176.62(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10322
